ZA200502944B - 2-Alkyl-(2-ammino-3-aryl-propionyl)-piperazine derivatives and related compounds as melanocortin receptor ligands for the treatment of obesity. - Google Patents
2-Alkyl-(2-ammino-3-aryl-propionyl)-piperazine derivatives and related compounds as melanocortin receptor ligands for the treatment of obesity. Download PDFInfo
- Publication number
- ZA200502944B ZA200502944B ZA200502944A ZA200502944A ZA200502944B ZA 200502944 B ZA200502944 B ZA 200502944B ZA 200502944 A ZA200502944 A ZA 200502944A ZA 200502944 A ZA200502944 A ZA 200502944A ZA 200502944 B ZA200502944 B ZA 200502944B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperazin
- ethyl
- oxo
- methyl
- substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 48
- 239000003446 ligand Substances 0.000 title claims description 26
- 208000008589 Obesity Diseases 0.000 title claims description 4
- 235000020824 obesity Nutrition 0.000 title claims description 4
- 108090000950 Melanocortin Receptors Proteins 0.000 title description 11
- 102000004378 Melanocortin Receptors Human genes 0.000 title description 11
- -1 4-flucrophenyl Chemical group 0.000 claims description 188
- 239000000203 mixture Substances 0.000 claims description 186
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- 239000001257 hydrogen Substances 0.000 claims description 117
- 229940080818 propionamide Drugs 0.000 claims description 96
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 78
- 125000000623 heterocyclic group Chemical group 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 51
- 239000000460 chlorine Substances 0.000 claims description 49
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 46
- 229910052794 bromium Inorganic materials 0.000 claims description 42
- 229910052801 chlorine Inorganic materials 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000004429 atom Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 31
- 125000002837 carbocyclic group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 14
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
- 125000006416 CBr Chemical group BrC* 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
- 230000006399 behavior Effects 0.000 claims description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000006414 CCl Chemical group ClC* 0.000 claims description 5
- 102100033668 Cartilage matrix protein Human genes 0.000 claims description 5
- 101001018382 Homo sapiens Cartilage matrix protein Proteins 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 230000036772 blood pressure Effects 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 230000009593 intrauterine fetal growth Effects 0.000 claims description 5
- 230000013016 learning Effects 0.000 claims description 5
- 230000015654 memory Effects 0.000 claims description 5
- 210000005036 nerve Anatomy 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 230000018052 penile erection Effects 0.000 claims description 5
- 230000008439 repair process Effects 0.000 claims description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims description 3
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 116
- BWKMGYQJPOAASG-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CNC(C(=O)O)CC2=C1 BWKMGYQJPOAASG-UHFFFAOYSA-N 0.000 claims 26
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 claims 20
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 8
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims 7
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- ZCLBLSZZIRMCLZ-UHFFFAOYSA-N 1-(methylamino)cyclopropane-1-carboxylic acid Chemical compound CNC1(C(O)=O)CC1 ZCLBLSZZIRMCLZ-UHFFFAOYSA-N 0.000 claims 5
- 241000282412 Homo Species 0.000 claims 5
- 206010006187 Breast cancer Diseases 0.000 claims 4
- 208000026310 Breast neoplasm Diseases 0.000 claims 4
- 206010008342 Cervix carcinoma Diseases 0.000 claims 4
- 206010009944 Colon cancer Diseases 0.000 claims 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims 4
- 206010014733 Endometrial cancer Diseases 0.000 claims 4
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 4
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims 4
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 4
- 201000005569 Gout Diseases 0.000 claims 4
- 206010020112 Hirsutism Diseases 0.000 claims 4
- 206010020772 Hypertension Diseases 0.000 claims 4
- 206010021138 Hypovolaemic shock Diseases 0.000 claims 4
- 206010022489 Insulin Resistance Diseases 0.000 claims 4
- 208000037093 Menstruation Disturbances Diseases 0.000 claims 4
- 206010028289 Muscle atrophy Diseases 0.000 claims 4
- 206010033128 Ovarian cancer Diseases 0.000 claims 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 4
- 206010060862 Prostate cancer Diseases 0.000 claims 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 4
- 208000030934 Restrictive pulmonary disease Diseases 0.000 claims 4
- 206010040047 Sepsis Diseases 0.000 claims 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims 4
- 208000001435 Thromboembolism Diseases 0.000 claims 4
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 4
- 230000001269 cardiogenic effect Effects 0.000 claims 4
- 206010007625 cardiogenic shock Diseases 0.000 claims 4
- 230000009084 cardiovascular function Effects 0.000 claims 4
- 201000010881 cervical cancer Diseases 0.000 claims 4
- 208000029742 colonic neoplasm Diseases 0.000 claims 4
- 208000029078 coronary artery disease Diseases 0.000 claims 4
- 230000007812 deficiency Effects 0.000 claims 4
- 201000010175 gallbladder cancer Diseases 0.000 claims 4
- 208000020694 gallbladder disease Diseases 0.000 claims 4
- 208000000509 infertility Diseases 0.000 claims 4
- 230000036512 infertility Effects 0.000 claims 4
- 231100000535 infertility Toxicity 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 231100000544 menstrual irregularity Toxicity 0.000 claims 4
- 125000005394 methallyl group Chemical group 0.000 claims 4
- 230000020763 muscle atrophy Effects 0.000 claims 4
- 201000000585 muscular atrophy Diseases 0.000 claims 4
- 201000008482 osteoarthritis Diseases 0.000 claims 4
- 239000002464 receptor antagonist Substances 0.000 claims 4
- 229940044551 receptor antagonist Drugs 0.000 claims 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims 4
- 206010040560 shock Diseases 0.000 claims 4
- 230000036528 appetite Effects 0.000 claims 3
- 235000019789 appetite Nutrition 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 201000002859 sleep apnea Diseases 0.000 claims 3
- ROWMQJJMCWDJDT-UHFFFAOYSA-N tribromomethane Chemical compound Br[C](Br)Br ROWMQJJMCWDJDT-UHFFFAOYSA-N 0.000 claims 3
- 125000004477 1-amino-cycloprop-1-yl group Chemical group NC1(CC1)* 0.000 claims 2
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 claims 2
- 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004803 chlorobenzyl group Chemical group 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004263 tetrahydroisoquinolin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])C2=C([H])C([H])=C([H])C([H])=C2C1([H])* 0.000 claims 2
- VHJNUODKRYWBAU-UHFFFAOYSA-N 1-amino-n-[1-[4-[3-(3,4-dichlorophenyl)-1-(methylamino)-1-oxopropan-2-yl]-2-ethylpiperazin-1-yl]-3-(4-fluorophenyl)-1-oxopropan-2-yl]cyclopropane-1-carboxamide Chemical compound CCC1CN(C(CC=2C=C(Cl)C(Cl)=CC=2)C(=O)NC)CCN1C(=O)C(NC(=O)C1(N)CC1)CC1=CC=C(F)C=C1 VHJNUODKRYWBAU-UHFFFAOYSA-N 0.000 claims 1
- QSJKTPLQMQLDLC-UHFFFAOYSA-N 2-[3-ethyl-4-[3-(4-fluorophenyl)-2-[(2-methoxyacetyl)amino]propanoyl]piperazin-1-yl]-n-methyl-3-naphthalen-2-ylpropanamide Chemical compound CCC1CN(C(CC=2C=C3C=CC=CC3=CC=2)C(=O)NC)CCN1C(=O)C(NC(=O)COC)CC1=CC=C(F)C=C1 QSJKTPLQMQLDLC-UHFFFAOYSA-N 0.000 claims 1
- MPSCIZSVICVEHU-UHFFFAOYSA-N 2-[4-[2-amino-3-(4-chlorophenyl)propanoyl]-3-(methoxymethyl)piperazin-1-yl]-3-(2-chlorophenyl)-n-methylpropanamide Chemical compound C1CN(C(=O)C(N)CC=2C=CC(Cl)=CC=2)C(COC)CN1C(C(=O)NC)CC1=CC=CC=C1Cl MPSCIZSVICVEHU-UHFFFAOYSA-N 0.000 claims 1
- KDTCYTVXRVMQBD-UHFFFAOYSA-N 2-[4-[2-amino-3-(4-chlorophenyl)propanoyl]-3-ethyl-2-oxopiperazin-1-yl]-n-methyl-3-naphthalen-2-ylpropanamide Chemical compound C1CN(C(CC=2C=C3C=CC=CC3=CC=2)C(=O)NC)C(=O)C(CC)N1C(=O)C(N)CC1=CC=C(Cl)C=C1 KDTCYTVXRVMQBD-UHFFFAOYSA-N 0.000 claims 1
- FBIBREHNRFMLIZ-UHFFFAOYSA-N 2-[4-[2-amino-3-(4-fluorophenyl)propanoyl]-2-oxo-3-propylpiperazin-1-yl]-n-methyl-3-naphthalen-2-ylpropanamide Chemical compound C1CN(C(CC=2C=C3C=CC=CC3=CC=2)C(=O)NC)C(=O)C(CCC)N1C(=O)C(N)CC1=CC=C(F)C=C1 FBIBREHNRFMLIZ-UHFFFAOYSA-N 0.000 claims 1
- OHRKZQRENWCBAO-UHFFFAOYSA-N 2-amino-n-[1-[4-[3-(4-chlorophenyl)-1-(methylamino)-1-oxopropan-2-yl]-2-methylpiperazin-1-yl]-3-(4-fluorophenyl)-1-oxopropan-2-yl]-2-methylpropanamide Chemical compound C1CN(C(=O)C(CC=2C=CC(F)=CC=2)NC(=O)C(C)(C)N)C(C)CN1C(C(=O)NC)CC1=CC=C(Cl)C=C1 OHRKZQRENWCBAO-UHFFFAOYSA-N 0.000 claims 1
- RRILCZSBZXEZHM-UHFFFAOYSA-N 2-amino-n-[3-(4-fluorophenyl)-1-[2-methoxy-3-methyl-4-[1-(methylamino)-3-naphthalen-2-yl-1-oxopropan-2-yl]piperazin-1-yl]-1-oxopropan-2-yl]-2-methylpropanamide Chemical compound C=1C=C2C=CC=CC2=CC=1CC(C(=O)NC)N(C(C1OC)C)CCN1C(=O)C(NC(=O)C(C)(C)N)CC1=CC=C(F)C=C1 RRILCZSBZXEZHM-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- WZKWKHWVCYDURW-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-[4-[2-[[2-(dimethylamino)acetyl]amino]-3-(4-fluorophenyl)propanoyl]-3-methylpiperazin-1-yl]-n-methylpropanamide Chemical compound C1CN(C(=O)C(CC=2C=CC(F)=CC=2)NC(=O)CN(C)C)C(C)CN1C(C(=O)NC)CC1=CC=C(Cl)C(Cl)=C1 WZKWKHWVCYDURW-UHFFFAOYSA-N 0.000 claims 1
- DSGKJUJXUYMLKZ-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-[4-[3-(4-fluorophenyl)-2-[2-(methylamino)propanoylamino]propanoyl]-3-methylpiperazin-1-yl]-n-methylpropanamide Chemical compound C1CN(C(CC=2C=C(Cl)C(Cl)=CC=2)C(=O)NC)CC(C)N1C(=O)C(NC(=O)C(C)NC)CC1=CC=C(F)C=C1 DSGKJUJXUYMLKZ-UHFFFAOYSA-N 0.000 claims 1
- PQJQYGWKSLEJNB-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-[4-[3-(4-fluorophenyl)-2-(methylamino)propanoyl]-3-methoxy-2-methylpiperazin-1-yl]-n-(2,2,2-trifluoroethyl)propanamide Chemical compound C1CN(C(CC=2C=CC(Cl)=CC=2)C(=O)NCC(F)(F)F)C(C)C(OC)N1C(=O)C(NC)CC1=CC=C(F)C=C1 PQJQYGWKSLEJNB-UHFFFAOYSA-N 0.000 claims 1
- DRNGLYHKYPNTEA-UHFFFAOYSA-N 4-azaniumylcyclohexane-1-carboxylate Chemical compound NC1CCC(C(O)=O)CC1 DRNGLYHKYPNTEA-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- MJGBOFOZSAEULI-UHFFFAOYSA-N 5-oxopyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCC(=O)N1.OC(=O)C1CCC(=O)N1 MJGBOFOZSAEULI-UHFFFAOYSA-N 0.000 claims 1
- IADUEWIQBXOCDZ-VKHMYHEASA-N Azetidine-2-carboxylic acid Natural products OC(=O)[C@@H]1CCN1 IADUEWIQBXOCDZ-VKHMYHEASA-N 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 claims 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims 1
- 239000011717 all-trans-retinol Substances 0.000 claims 1
- 208000008784 apnea Diseases 0.000 claims 1
- GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- HSXWATNROHQVDG-UHFFFAOYSA-N n-[1-[4-[3-(3-chlorophenyl)-1-(methylamino)-1-oxopropan-2-yl]-2-propylpiperazin-1-yl]-3-(4-fluorophenyl)-1-oxopropan-2-yl]-2-hydroxy-2-methylpropanamide Chemical compound CCCC1CN(C(CC=2C=C(Cl)C=CC=2)C(=O)NC)CCN1C(=O)C(NC(=O)C(C)(C)O)CC1=CC=C(F)C=C1 HSXWATNROHQVDG-UHFFFAOYSA-N 0.000 claims 1
- IZNIAVGKDIAERZ-UHFFFAOYSA-N n-[1-[4-[3-(4-chlorophenyl)-1-(methylamino)-1-oxopropan-2-yl]-2-propylpiperazin-1-yl]-3-(4-fluorophenyl)-1-oxopropan-2-yl]-1-(methylamino)cyclopropane-1-carboxamide Chemical compound CCCC1CN(C(CC=2C=CC(Cl)=CC=2)C(=O)NC)CCN1C(=O)C(NC(=O)C1(CC1)NC)CC1=CC=C(F)C=C1 IZNIAVGKDIAERZ-UHFFFAOYSA-N 0.000 claims 1
- OSNMRQIMBWNWLM-UHFFFAOYSA-N n-[3-(4-chlorophenyl)-1-[4-(2-naphthalen-2-ylethyl)-3-oxo-2-propylpiperazin-1-yl]-1-oxopropan-2-yl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C1CN(CCC=2C=C3C=CC=CC3=CC=2)C(=O)C(CCC)N1C(=O)C(NC(=O)C1NCC2=CC=CC=C2C1)CC1=CC=C(Cl)C=C1 OSNMRQIMBWNWLM-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 235000019172 retinyl palmitate Nutrition 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 102000005962 receptors Human genes 0.000 description 18
- 108020003175 receptors Proteins 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- 108010008364 Melanocortins Proteins 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002865 melanocortin Substances 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical group 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 101150065749 Churc1 gene Proteins 0.000 description 4
- 102100038239 Protein Churchill Human genes 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- BUPDPLXLAKNJMI-ZETCQYMHSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC=C BUPDPLXLAKNJMI-ZETCQYMHSA-N 0.000 description 3
- 101800000414 Corticotropin Proteins 0.000 description 3
- 102400000739 Corticotropin Human genes 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 108010007013 Melanocyte-Stimulating Hormones Proteins 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 3
- 229960000258 corticotropin Drugs 0.000 description 3
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- RRCSZIDKASXGKD-SFTDATJTSA-N methyl (2s)-3-naphthalen-2-yl-2-[[(2s)-2-[(2-nitrophenyl)sulfonylamino]pent-4-enoyl]amino]propanoate Chemical compound N([C@@H](CC=C)C(=O)N[C@@H](CC=1C=C2C=CC=CC2=CC=1)C(=O)OC)S(=O)(=O)C1=CC=CC=C1[N+]([O-])=O RRCSZIDKASXGKD-SFTDATJTSA-N 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 2
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 2
- 239000000637 Melanocyte-Stimulating Hormone Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000005275 alkylenearyl group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- WJJRDQQSLKFKAM-OALUTQOASA-N methyl (2s)-3-naphthalen-2-yl-2-[(3s)-2-oxo-3-prop-2-enylpiperazin-1-yl]propanoate Chemical compound N1([C@@H](CC=2C=C3C=CC=CC3=CC=2)C(=O)OC)CCN[C@@H](CC=C)C1=O WJJRDQQSLKFKAM-OALUTQOASA-N 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- BUPDPLXLAKNJMI-SSDOTTSWSA-N (2r)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)CC=C BUPDPLXLAKNJMI-SSDOTTSWSA-N 0.000 description 1
- BLBURMVCRKOOEK-CQSZACIVSA-N (2r)-2-amino-2-[(2,4-difluorophenyl)methyl]-3-[(2-methylpropan-2-yl)oxy]-3-oxopropanoic acid Chemical compound CC(C)(C)OC(=O)[C@](N)(C(O)=O)CC1=CC=C(F)C=C1F BLBURMVCRKOOEK-CQSZACIVSA-N 0.000 description 1
- VRLRBZQHULDJAK-CQSZACIVSA-N (2r)-2-amino-2-[(3-fluorophenyl)methyl]-3-[(2-methylpropan-2-yl)oxy]-3-oxopropanoic acid Chemical compound CC(C)(C)OC(=O)[C@](N)(C(O)=O)CC1=CC=CC(F)=C1 VRLRBZQHULDJAK-CQSZACIVSA-N 0.000 description 1
- UILSMNBVJDLMCU-CQSZACIVSA-N (2r)-2-amino-2-[(4-hydroxyphenyl)methyl]-3-[(2-methylpropan-2-yl)oxy]-3-oxopropanoic acid Chemical compound CC(C)(C)OC(=O)[C@](N)(C(O)=O)CC1=CC=C(O)C=C1 UILSMNBVJDLMCU-CQSZACIVSA-N 0.000 description 1
- SSLWXONUCQDGQZ-OAHLLOKOSA-N (2r)-2-amino-2-[(4-methylphenyl)methyl]-3-[(2-methylpropan-2-yl)oxy]-3-oxopropanoic acid Chemical compound CC1=CC=C(C[C@@](N)(C(O)=O)C(=O)OC(C)(C)C)C=C1 SSLWXONUCQDGQZ-OAHLLOKOSA-N 0.000 description 1
- RDIZQXGXLJATEI-CQSZACIVSA-N (2r)-2-amino-3-[(2-methylpropan-2-yl)oxy]-3-oxo-2-[[4-(trifluoromethyl)phenyl]methyl]propanoic acid Chemical compound CC(C)(C)OC(=O)[C@](N)(C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 RDIZQXGXLJATEI-CQSZACIVSA-N 0.000 description 1
- BETBOAZCLSJOBQ-LLVKDONJSA-N (2r)-3-(4-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)CC1=CC=C(Cl)C=C1 BETBOAZCLSJOBQ-LLVKDONJSA-N 0.000 description 1
- RCXSXRAUMLKRRL-LLVKDONJSA-N (2r)-3-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)CC1=CC=C(F)C=C1 RCXSXRAUMLKRRL-LLVKDONJSA-N 0.000 description 1
- PNFVIPIQXAIUAY-LURJTMIESA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC[C@@H](C(O)=O)NC(=O)OC(C)(C)C PNFVIPIQXAIUAY-LURJTMIESA-N 0.000 description 1
- QVHJQCGUWFKTSE-YFKPBYRVSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)OC(C)(C)C QVHJQCGUWFKTSE-YFKPBYRVSA-N 0.000 description 1
- BHLYWTBLPOXSJF-MUEKUWCCSA-N (2s)-2-[(3s)-4-[(2r)-2-amino-3-(4-chlorophenyl)propanoyl]-3-methyl-2-oxopiperazin-1-yl]-n-methyl-3-naphthalen-2-ylpropanamide Chemical compound C([C@@H](N)C(=O)N1CCN(C([C@@H]1C)=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)C(=O)NC)C1=CC=C(Cl)C=C1 BHLYWTBLPOXSJF-MUEKUWCCSA-N 0.000 description 1
- GKRRTFCDSZGFSZ-QMMMGPOBSA-N (2s)-3-cyclopropyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1CC1 GKRRTFCDSZGFSZ-QMMMGPOBSA-N 0.000 description 1
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 description 1
- WPOPFTKMUDIAOZ-UHFFFAOYSA-N 2-(butoxycarbonylamino)pentanoic acid Chemical compound CCCCOC(=O)NC(C(O)=O)CCC WPOPFTKMUDIAOZ-UHFFFAOYSA-N 0.000 description 1
- BUPDPLXLAKNJMI-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC=C BUPDPLXLAKNJMI-UHFFFAOYSA-N 0.000 description 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 125000003974 3-carbamimidamidopropyl group Chemical group C(N)(=N)NCCC* 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000000275 Adrenocorticotropic Hormone Substances 0.000 description 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 108010088565 Melanocortin 5 receptor Proteins 0.000 description 1
- 102000030612 Melanocortin 5 receptor Human genes 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 108091036732 NRON Proteins 0.000 description 1
- 208000012641 Pigmentation disease Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100027467 Pro-opiomelanocortin Human genes 0.000 description 1
- 102000003946 Prolactin Human genes 0.000 description 1
- 108010057464 Prolactin Proteins 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 108010021428 Type 1 Melanocortin Receptor Proteins 0.000 description 1
- 108010021430 Type 2 Melanocortin Receptor Proteins 0.000 description 1
- 108010021433 Type 3 Melanocortin Receptor Proteins 0.000 description 1
- 102000008318 Type 3 Melanocortin Receptor Human genes 0.000 description 1
- 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 description 1
- 102000008316 Type 4 Melanocortin Receptor Human genes 0.000 description 1
- 206010046788 Uterine haemorrhage Diseases 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 230000006583 body weight regulation Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000008344 brain blood flow Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 208000001901 epithelial recurrent erosion dystrophy Diseases 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 230000004634 feeding behavior Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000000185 intracerebroventricular administration Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- JODMJDRLZIAIOQ-NGDRWEMDSA-N methyl (2s)-2-[(3s)-4-[(2r)-3-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-2-oxo-3-prop-2-enylpiperazin-1-yl]-3-naphthalen-2-ylpropanoate Chemical compound C([C@H](C(=O)N1CCN(C([C@@H]1CC=C)=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)C(=O)OC)NC(=O)OC(C)(C)C)C1=CC=C(F)C=C1 JODMJDRLZIAIOQ-NGDRWEMDSA-N 0.000 description 1
- HYHJBLALWIIOFU-PMACEKPBSA-N methyl (2s)-2-[[(2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoyl]amino]-3-naphthalen-2-ylpropanoate Chemical compound C1=CC=CC2=CC(C[C@@H](C(=O)OC)NC(=O)[C@H](CC=C)NC(=O)OC(C)(C)C)=CC=C21 HYHJBLALWIIOFU-PMACEKPBSA-N 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000003585 oxepinyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000037324 pain perception Effects 0.000 description 1
- 230000032696 parturition Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical group O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000028742 placenta development Effects 0.000 description 1
- 230000012495 positive regulation of renal sodium excretion Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003236 pyrrolines Chemical class 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000021595 spermatogenesis Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000006442 vascular tone Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42057802P | 2002-10-23 | 2002-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200502944B true ZA200502944B (en) | 2006-02-22 |
Family
ID=32176593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200502944A ZA200502944B (en) | 2002-10-23 | 2005-04-12 | 2-Alkyl-(2-ammino-3-aryl-propionyl)-piperazine derivatives and related compounds as melanocortin receptor ligands for the treatment of obesity. |
Country Status (18)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2574156A1 (en) | 2004-07-19 | 2006-02-23 | Merck & Co., Inc. | Acylated piperidine derivatives as melanocortin-4 receptor agonists |
| AU2007283113A1 (en) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use |
| US8163779B2 (en) | 2006-12-20 | 2012-04-24 | Takeda San Diego, Inc. | Glucokinase activators |
| US8173645B2 (en) * | 2007-03-21 | 2012-05-08 | Takeda San Diego, Inc. | Glucokinase activators |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| KR101478253B1 (ko) * | 2007-09-17 | 2014-12-31 | 국민대학교산학협력단 | 아룸 팔래스티눔(Ａｒｕｍ ｐａｌａｅｓｔｉｎｕｎＢｏｉｓｓ) 유래 항암용 피페라지움 화합물 |
| AR072707A1 (es) | 2008-07-09 | 2010-09-15 | Sanofi Aventis | Compuestos heterociclicos, procesos para su preparacion, medicamentos que comprenden estos compuestos y el uso de los mismos |
| EP2358200A4 (en) | 2008-11-17 | 2012-05-16 | Merck Sharp & Dohme | BICYCLIC AMINES SUBSTITUTED FOR THE TREATMENT OF DIABETES |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| WO2011011506A1 (en) | 2009-07-23 | 2011-01-27 | Schering Corporation | Spirocyclic oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors |
| WO2011011508A1 (en) | 2009-07-23 | 2011-01-27 | Schering Corporation | Benzo-fused oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors |
| US20110034469A1 (en) | 2009-08-04 | 2011-02-10 | Takeda Pharmaceutical Company Limited | Heterocyclic Compound |
| ES2443016T3 (es) | 2009-08-26 | 2014-02-17 | Sanofi | Nuevos hidratos cristalinos de fluoroglicósidos heteroaromáticos, productos farmacéuticos que comprenden estos compuestos, y su empleo |
| WO2011137024A1 (en) | 2010-04-26 | 2011-11-03 | Merck Sharp & Dohme Corp. | Novel spiropiperidine prolylcarboxypeptidase inhibitors |
| US9365539B2 (en) | 2010-05-11 | 2016-06-14 | Merck Sharp & Dohme Corp. | Prolylcarboxypeptidase inhibitors |
| WO2011156246A1 (en) | 2010-06-11 | 2011-12-15 | Merck Sharp & Dohme Corp. | Novel prolylcarboxypeptidase inhibitors |
| WO2012120051A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8901114B2 (en) | 2011-03-08 | 2014-12-02 | Sanofi | Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| US9321749B1 (en) * | 2012-07-25 | 2016-04-26 | Globavir Biosciences, Inc. | Heterocyclic compounds and uses thereof |
| AU2016302648A1 (en) * | 2015-08-04 | 2018-02-22 | Astellas Pharma Inc. | Piperazine derivative |
Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4251438A (en) * | 1979-06-14 | 1981-02-17 | The Upjohn Company | Piperazinone and piperazine polypeptides |
| US5578593A (en) | 1992-12-11 | 1996-11-26 | Merck & Co., Inc. | Spiro piperidines and homologs promote release of growth hormone |
| RU2168512C2 (ru) | 1992-12-11 | 2001-06-10 | Мерк Энд Ко., Инк. | Спиропиперидины, способы их получения (варианты) |
| US5556853A (en) * | 1993-10-29 | 1996-09-17 | Takeda Chemical Industries, Ltd. | Epoxysuccinic acid derivatives |
| US5494919A (en) * | 1993-11-09 | 1996-02-27 | Merck & Co., Inc. | 2-substituted piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone |
| US5492916A (en) * | 1993-12-23 | 1996-02-20 | Merck & Co., Inc. | Di- and tri-substituted piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone |
| US5721251A (en) * | 1993-12-10 | 1998-02-24 | Merck & Co., Inc. | Piperidine, pyrrolidine and hexahydro-1H-azepines promote release of growth hormone |
| US5721250A (en) * | 1993-12-23 | 1998-02-24 | Merck & Co. Inc. | Di-and tri-substituted piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone |
| WO1996002530A1 (en) | 1994-07-20 | 1996-02-01 | Merck & Co., Inc. | Piperidines and hexahydro-1h-azepines spiro substituted at the 4-position promote release of growth hormone |
| US5767118A (en) | 1994-10-26 | 1998-06-16 | Merck & Co., Inc. | 4-Heterocyclic peperidines promote release of growth hormone |
| US5889006A (en) | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| IL117798A (en) | 1995-04-07 | 2001-11-25 | Schering Plough Corp | Tricyclic compounds useful for inhibiting the function of protein - G and for the treatment of malignant diseases, and pharmaceutical preparations containing them |
| ATE288444T1 (de) | 1995-05-29 | 2005-02-15 | Pfizer | Dipeptide, die die ausschüttung von wachstumshormonen stimulieren |
| GB9612276D0 (en) * | 1996-06-12 | 1996-08-14 | Merck & Co Inc | 4-Spiroindoline piperidines promote release of growth hormone |
| US5804578A (en) * | 1996-04-03 | 1998-09-08 | Merck & Co., Inc. | Piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone |
| US5877182A (en) * | 1996-09-13 | 1999-03-02 | Merck & Co., Inc. | Piperidines promote release of growth hormone |
| WO1998010653A1 (en) | 1996-09-13 | 1998-03-19 | Merck & Co., Inc. | Piperidines, pyrrolidines and hexahydro-1h-azepines promote release of growth hormone |
| US5965565A (en) * | 1996-12-12 | 1999-10-12 | Merck & Co., Inc. | Piperidines promote release of growth hormone |
| GB9709972D0 (en) | 1997-05-19 | 1997-07-09 | Pfizer Ltd | Tetrazoles |
| WO1999055679A1 (en) | 1998-04-28 | 1999-11-04 | Trega Biosciences, Inc. | Isoquinoline compound melanocortin receptor ligands and methods of using same |
| CA2329881C (en) | 1998-05-11 | 2010-03-16 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| WO1999064002A1 (en) | 1998-06-11 | 1999-12-16 | Merck & Co., Inc. | Spiropiperidine derivatives as melanocortin receptor agonists |
| US6294534B1 (en) * | 1998-06-11 | 2001-09-25 | Merck & Co., Inc. | Spiropiperidine derivatives as melanocortin receptor agonists |
| KR100660309B1 (ko) | 1998-09-22 | 2006-12-22 | 아스텔라스세이야쿠 가부시키가이샤 | 시아노페닐 유도체 |
| CA2371583C (en) | 1999-05-04 | 2005-09-13 | Schering Corporation | Piperazine derivatives useful as ccr5 antagonists |
| WO2000074679A1 (en) | 1999-06-04 | 2000-12-14 | Merck & Co., Inc. | Substituted piperidines as melanocortin-4 receptor agonists |
| AU6000200A (en) | 1999-07-16 | 2001-02-05 | Biocompatibles Limited | Braided stent |
| US6472398B1 (en) | 2000-03-23 | 2002-10-29 | Merck & Co., Inc. | Spiropiperidine derivatives as melanocortin receptor agonists |
| CA2403686C (en) | 2000-03-23 | 2010-01-26 | Merck & Co., Inc. | Substituted piperidines as melanocortin receptor agonists |
| EP1289526A4 (en) | 2000-05-30 | 2005-03-16 | Merck & Co Inc | MELANOCORTIN RECEPTOR AGONISTS |
| AU2001260548A1 (en) | 2000-06-28 | 2002-01-08 | Pfizer Products Inc. | Melanocortin receptor ligands |
| AU2001288285B2 (en) | 2000-08-23 | 2005-09-29 | Merck & Co., Inc. | Substituted piperidines as melanocortin receptor agonists |
| US6573264B1 (en) | 2000-10-23 | 2003-06-03 | Cv Therapeutics, Inc. | Heteroaryl alkyl piperazine derivatives |
| GB0030710D0 (en) | 2000-12-15 | 2001-01-31 | Hoffmann La Roche | Piperazine derivatives |
| EP1368339A1 (en) | 2001-01-23 | 2003-12-10 | Eli Lilly & Company | Substituted piperidines/piperazines as melanocortin receptor agonists |
| DE60205465T2 (de) | 2001-01-23 | 2006-04-20 | Eli Lilly And Co., Indianapolis | Piperazinderivate als agonisten des melanocortin-rezeptors |
| JP2004524297A (ja) | 2001-01-23 | 2004-08-12 | イーライ・リリー・アンド・カンパニー | メラノコルチン受容体アゴニスト |
| ES2283550T3 (es) | 2001-02-28 | 2007-11-01 | MERCK & CO., INC. | Derivados de piperidina acilados como antagonistas del receptor de. |
| WO2002068387A2 (en) | 2001-02-28 | 2002-09-06 | Merck & Co., Inc. | Acylated piperidine derivatives as melanocortin-4 receptor agonists |
| EP1363631A4 (en) | 2001-03-02 | 2005-11-16 | Bristol Myers Squibb Co | "COMPOUNDS SUITED AS MODULATORS OF MELANOCORTIN RECEPTORS AND THESE PHARMACEUTICAL COMPOSITIONS CONTAINING THEREOF" |
| US6900329B2 (en) | 2001-03-21 | 2005-05-31 | Schering Corporation | MCH antagonists and their use in the treatment of obesity |
| DK1373256T3 (da) | 2001-03-29 | 2005-10-10 | Schering Corp | CCR5-antagonister, der er nyttige til behandling af AIDS |
| US6911447B2 (en) | 2001-04-25 | 2005-06-28 | The Procter & Gamble Company | Melanocortin receptor ligands |
| US7115607B2 (en) | 2001-07-25 | 2006-10-03 | Amgen Inc. | Substituted piperazinyl amides and methods of use |
| US7354923B2 (en) * | 2001-08-10 | 2008-04-08 | Palatin Technologies, Inc. | Piperazine melanocortin-specific compounds |
| AU2002331064B2 (en) | 2001-08-10 | 2007-08-23 | Palatin Technologies, Inc. | Peptidomimetics of biologically active metallopeptides |
| DE60217363T2 (de) | 2001-09-06 | 2007-10-11 | Schering Corp. | 17beta-hydroxysteroid dehydrogenase type 3 inhibitoren zur behandlung von androgen-abhängigen erkrankungen |
| WO2003031410A1 (en) | 2001-10-09 | 2003-04-17 | Neurocrine Biosciences, Inc. | Ligands of melanocortin receptors and compositions and methods related thereto |
| CN1575283A (zh) | 2001-10-22 | 2005-02-02 | 辉瑞产品公司 | 具有ccr1受体拮抗剂活性的哌嗪衍生物 |
| WO2003061660A1 (en) | 2002-01-23 | 2003-07-31 | Eli Lilly And Company | Melanocortin receptor agonists |
-
2003
- 2003-10-20 US US10/689,022 patent/US7132539B2/en not_active Expired - Fee Related
- 2003-10-20 TW TW092129035A patent/TW200504033A/zh unknown
- 2003-10-22 BR BR0315614-1A patent/BR0315614A/pt not_active IP Right Cessation
- 2003-10-22 CA CA002501231A patent/CA2501231A1/en not_active Abandoned
- 2003-10-22 EP EP03777759A patent/EP1556361A2/en not_active Withdrawn
- 2003-10-22 PE PE2003001070A patent/PE20040778A1/es not_active Application Discontinuation
- 2003-10-22 AU AU2003286557A patent/AU2003286557A1/en not_active Abandoned
- 2003-10-22 RU RU2005111967/04A patent/RU2005111967A/ru not_active Application Discontinuation
- 2003-10-22 AR ARP030103859A patent/AR043054A1/es not_active Application Discontinuation
- 2003-10-22 JP JP2004546990A patent/JP2006506384A/ja active Pending
- 2003-10-22 MX MXPA05004378A patent/MXPA05004378A/es unknown
- 2003-10-22 PL PL376702A patent/PL376702A1/pl not_active Application Discontinuation
- 2003-10-22 CN CNA2003801009342A patent/CN1703221A/zh active Pending
- 2003-10-22 WO PCT/US2003/033402 patent/WO2004037797A2/en active Application Filing
- 2003-10-22 KR KR1020057006836A patent/KR20050072445A/ko not_active Application Discontinuation
-
2005
- 2005-04-12 ZA ZA200502944A patent/ZA200502944B/en unknown
- 2005-04-25 MA MA28235A patent/MA27478A1/fr unknown
- 2005-05-23 NO NO20052476A patent/NO20052476D0/no not_active Application Discontinuation
-
2006
- 2006-06-23 US US11/473,972 patent/US20060247224A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NO20052476L (no) | 2005-05-23 |
| JP2006506384A (ja) | 2006-02-23 |
| MXPA05004378A (es) | 2005-07-05 |
| WO2004037797A3 (en) | 2004-11-04 |
| KR20050072445A (ko) | 2005-07-11 |
| MA27478A1 (fr) | 2005-08-01 |
| CA2501231A1 (en) | 2004-05-06 |
| EP1556361A2 (en) | 2005-07-27 |
| PE20040778A1 (es) | 2004-12-21 |
| US7132539B2 (en) | 2006-11-07 |
| TW200504033A (en) | 2005-02-01 |
| NO20052476D0 (no) | 2005-05-23 |
| RU2005111967A (ru) | 2006-01-20 |
| WO2004037797A2 (en) | 2004-05-06 |
| AR043054A1 (es) | 2005-07-13 |
| BR0315614A (pt) | 2005-08-30 |
| PL376702A1 (pl) | 2006-01-09 |
| CN1703221A (zh) | 2005-11-30 |
| US20050010031A1 (en) | 2005-01-13 |
| US20060247224A1 (en) | 2006-11-02 |
| AU2003286557A1 (en) | 2004-05-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200502944B (en) | 2-Alkyl-(2-ammino-3-aryl-propionyl)-piperazine derivatives and related compounds as melanocortin receptor ligands for the treatment of obesity. | |
| ES2283550T3 (es) | Derivados de piperidina acilados como antagonistas del receptor de. | |
| ES2296968T3 (es) | Piperidinas sustituidas como moduladores del receptor de melanocortina. | |
| AU2004305079B2 (en) | 3-cycloalkylaminopyrrolidine derivatives as modulators of chemokine receptors | |
| KR100662309B1 (ko) | 멜라노코르틴 수용체 리간드 | |
| US20040053933A1 (en) | Ligands of melanocortin receptors and compositions and methods related thereto | |
| AU2006236622B2 (en) | Compositions of novel opioid compounds and method of use thereof | |
| CN102030750A (zh) | 用作CB1受体配体的新四氢-1H-吡啶并[4,3-b]吲哚衍生物 | |
| CA2377369A1 (en) | Substituted piperidines as melanocortin-4 receptor agonists | |
| JP2008518889A (ja) | 新規ブラジキニンｂ１アンタゴニスト、それらの製造方法及び薬物としてのそれらの使用 | |
| JP2005503369A (ja) | メラノコルチン受容体のモジュレーターとしての置換ピペラジン | |
| AU2002319695A1 (en) | Substituted piperidines as modulators of the melanocortin receptor | |
| AU2010306927A1 (en) | Amino - pyrimidine compounds as inhibitors of TBKL and/or IKK epsilon | |
| AU2009314827A1 (en) | Melanocortin receptor agonists | |
| CA2650914A1 (en) | Compounds that are agonists of muscarinic receptors and that may be effective in treating pain, alzheimer's disease and/or schizophrenia | |
| MX2013002011A (es) | Derivados ciclicos de carboxamida y urea sustituidos como ligandos del receptor vainiloide. | |
| CA2171850A1 (en) | Novel compound having platelet aggregation inhibitor effect | |
| WO2010065799A2 (en) | Amine substituted piperidine melanocortin receptor-specific compounds | |
| US20040204426A1 (en) | 4-Imidazolin-2-one compounds | |
| CA2636545A1 (en) | Urotensin ii receptor antagonists | |
| CA2483806A1 (en) | N-acyl piperidine derivatives for use as melanocortin receptor ligands in the treatment of feeding disorders | |
| CA2781858A1 (en) | Modulators of tnf-.alpha. signaling | |
| US20030236230A1 (en) | Melanocortin receptor ligands | |
| WO2010065800A1 (en) | Hydrazine substituted piperidine melanocortin receptor-specific compounds | |
| WO2010065801A1 (en) | Amine substituted piperazine melanocortin receptor-specific compounds |